JPS642625B2 - - Google Patents

Info

Publication number: JPS642625B2
Authority: JP; Japan
Prior art keywords: group; polyarylene sulfide; general formula; polymer; heterocycle
Prior art date: 1983-05-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

JP8151183A

Other languages

English (en)

Japanese (ja)

Other versions

JPS59206462A (ja

Inventor

Toshuki Asakura

Yasuhiko Mutaguchi

Hiroaki Kobayashi

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Toray Industries Inc

Original Assignee

Toray Industries Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-05-10

Filing date

1983-05-10

Publication date

1989-01-18

1983-05-10 Application filed by Toray Industries Inc filed Critical Toray Industries Inc

1983-05-10 Priority to JP8151183A priority Critical patent/JPS59206462A/ja

1984-11-22 Publication of JPS59206462A publication Critical patent/JPS59206462A/ja

1989-01-18 Publication of JPS642625B2 publication Critical patent/JPS642625B2/ja

Status Granted legal-status Critical Current

Links

UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 20
229920000412 polyarylene Polymers 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 11
125000000623 heterocyclic group Chemical group 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 10
125000003118 aryl group Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
229920000642 polymer Polymers 0.000 description 21
238000006116 polymerization reaction Methods 0.000 description 12
239000003513 alkali Substances 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
150000001491 aromatic compounds Chemical class 0.000 description 7
239000011593 sulfur Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
-1 p-phenylene, m-phenylene Chemical group 0.000 description 6
238000000034 method Methods 0.000 description 5
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
238000004040 coloring Methods 0.000 description 3
230000006866 deterioration Effects 0.000 description 3
239000007789 gas Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
230000000087 stabilizing effect Effects 0.000 description 2
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
UCTUNCJCTXXXGJ-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione;sodium Chemical compound [Na].C1=CC=C2NC(=S)NC2=C1 UCTUNCJCTXXXGJ-UHFFFAOYSA-N 0.000 description 1
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
YCFUHBHONRJFHI-UHFFFAOYSA-N 2,6-dichloronaphthalene Chemical compound C1=C(Cl)C=CC2=CC(Cl)=CC=C21 YCFUHBHONRJFHI-UHFFFAOYSA-N 0.000 description 1
YTBRNEUEFCNVHC-UHFFFAOYSA-N 4,4'-dichlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=C(Cl)C=C1 YTBRNEUEFCNVHC-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
239000004734 Polyphenylene sulfide Substances 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000011033 desalting Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
MSJMDZAOKORVFC-UAIGNFCESA-L disodium maleate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C/C([O-])=O MSJMDZAOKORVFC-UAIGNFCESA-L 0.000 description 1
239000010408 film Substances 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
229940031993 lithium benzoate Drugs 0.000 description 1
LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000069 polyphenylene sulfide Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229940077386 sodium benzenesulfonate Drugs 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
229940079101 sodium sulfide Drugs 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
ZGHLCBJZQLNUAZ-UHFFFAOYSA-N sodium sulfide nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[Na+].[S-2] ZGHLCBJZQLNUAZ-UHFFFAOYSA-N 0.000 description 1
229940048181 sodium sulfide nonahydrate Drugs 0.000 description 1
MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
WMDLZMCDBSJMTM-UHFFFAOYSA-M sodium;sulfanide;nonahydrate Chemical compound O.O.O.O.O.O.O.O.O.[Na+].[SH-] WMDLZMCDBSJMTM-UHFFFAOYSA-M 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000010409 thin film Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Compositions Of Macromolecular Compounds (AREA)

JP8151183A 1983-05-10 1983-05-10 ポリアリーレンスルフィド変性物の製造方法 Granted JPS59206462A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP8151183A JPS59206462A (ja)	1983-05-10	1983-05-10	ポリアリーレンスルフィド変性物の製造方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP8151183A JPS59206462A (ja)	1983-05-10	1983-05-10	ポリアリーレンスルフィド変性物の製造方法

Publications (2)

Publication Number	Publication Date
JPS59206462A JPS59206462A (ja)	1984-11-22
JPS642625B2 true JPS642625B2 (fr)	1989-01-18

Family

ID=13748375

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP8151183A Granted JPS59206462A (ja)	1983-05-10	1983-05-10	ポリアリーレンスルフィド変性物の製造方法

Country Status (1)

Country	Link
JP (1)	JPS59206462A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3339581A1 (de) *	1983-11-02	1985-05-09	Bayer Ag, 5090 Leverkusen	Polyarylensulfide mit verminderter korrosion
JPS6297821A (ja) *	1985-10-25	1987-05-07	Kureha Chem Ind Co Ltd	透明で着色の少ないポリアリーレンチオエーテル溶融成形物およびその製造法
JP5029506B2 (ja) *	2008-06-19	2012-09-19	東ソー株式会社	ポリアリーレンスルフィド組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5790018A (en) *	1980-11-27	1982-06-04	Toray Ind Inc	Stabilized polyphenylene sulfide and its production
JPS57164130A (en) *	1981-04-03	1982-10-08	Toray Ind Inc	Production of heat-resistant resin molding

1983
- 1983-05-10 JP JP8151183A patent/JPS59206462A/ja active Granted

Also Published As

Publication number	Publication date
JPS59206462A (ja)	1984-11-22

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